Sodium hydride → HCID 44128630, compound

HRID 1627600Notes

Reaction equation

HRID 1627600 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[H-].[Na+]>CN(C=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 38260554-Fluoro-2-methylbenzonitrile

Product 1

HCID 44128630HCID 44128630, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.35 g 4-Fluoro-2-methyl-benzonitrile, dissolved in DMF, was added to 2.11 g 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester and 0.6 g sodium hydride in 30 mL DMF. The mixture was stirred at room temperature (rt) until the reaction was complete. The reaction was quenched with water. The aqueous layer was extracted with ethylacetate (AcOEt) or methyl tert. butyl ether (MTB ether). The combined organic layers were washed with brine, dried and concentrated to give 2.6 g (yield 81%) 4-(4-Cyano-3-methyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. Mass: (C18H24N2O3): calcd. 316. found 261 [M+H−t(C4H9)]+

Workup

  1. customThe reaction was quenched with water
  2. extractionThe aqueous layer was extracted with ethylacetate (AcOEt) or methyl tert. butyl ether (MTB ether)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40a32370e28043f69c78afac3274e4fd
Source dataset
uspto-grants-2014_07
Patent number
US08785642B2

Reaction notes

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